Two New Coumarins from the Chloroform Extract of Angelica urumiensis from Iran

Mohammadi, Mehdi; Yousefi, Maryam; Habibi, Zohreh; Shafiee, Abbas

doi:10.1248/cpb.58.546

Cited by 15 publications

(5 citation statements)

References 11 publications

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“…Such stereoisomers oftentimes exhibit very similar MS/MS spectra and is the reason that NAP annotates at the level of molecular families without considering retention time or other information that would differentiate among isomers. Candidate structures annotated by NAP were as follows: mezerein for m / z 653.257, dadahol B for m / z 667.218, threo -carolignan K for m / z 697.229, a pyranocoumarin dimer for m / z 669.234, and syringaresinol 4- O -apiofuranosyl-(1→2)-glucopyranoside for m / z 727.244. All of these metabolites have not been commonly observed from plants, and none of these have been previously isolated from Sageretia species or other Rhamnaceae plants.…”

Section: Results and Discussionmentioning

confidence: 99%

Targeted Isolation of Neuroprotective Dicoumaroyl Neolignans and Lignans from Sageretia theezans Using in Silico Molecular Network Annotation Propagation-Based Dereplication

et al. 2018

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The integration of LC-MS/MS molecular networking and in silico MS/MS fragmentation is an emerging method for dereplication of natural products. In the present study, a targeted isolation of natural products using a new in silico-based annotation tool named Network Annotation Propagation (NAP) is described. NAP improves accuracy of in silico fragmentation analyses by reranking candidate structures based on the network topology from MS/MS-based molecular networking. Annotation for the MS/MS spectral network of the Sageratia theezans twig extract was performed using NAP, and most molecular families within the network, including the known triterpenoids 1-7, could be putatively annotated, without relying on any previous reports of molecules from this species. Based on the in silico dereplication results, molecules were prioritized for isolation. In total, six dicoumaroyl 8- O-4' neolignans (8-13) and three dicoumaroyl lignans (14-16) were isolated from the twigs of S. theezans and structurally characterized by spectroscopic analyses. Isolates were evaluated for their neuroprotective activity, and compounds 14-16 showed potent protective effects against glutamate-induced oxidative stress in mouse HT22 cells at a concentration of 12.5 μM.

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Section: Results and Discussionmentioning

confidence: 99%

Targeted Isolation of Neuroprotective Dicoumaroyl Neolignans and Lignans from Sageretia theezans Using in Silico Molecular Network Annotation Propagation-Based Dereplication

et al. 2018

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“…The three fractions were individually evaporated under vacuum till dryness was achieved to give hexane fraction dry weight (10 g), CHCl 3 (5.57 g), EtOAc fraction (3.54 g), and ethanol (8.21 g). The CHCl 3 was chosen for further isolation based on Thin-Layer Chromatography (TLC) spotting results and by comparing the published data [9,35,36]. Further fractionation was performed under Vacuum Liquid Chromatography (VLC).…”

Section: Fractionation and Purificationmentioning

confidence: 99%

Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of Ammi majus Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin

Fathallah,

El Deeb,

Rabea

et al. 2023

Metabolites

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Ammi majus, a well-established member of the Umbelliferae (Apiaceae) family, is endogenous to Egypt. The main parts of this plant that are used are the fruits, which contain coumarins and flavonoids as major active constituents. The roots are usually considered by-products that are discarded and not fed to cattle because of coumarins’ potential toxicity. The goal of this study was to ensure the sustainability of the plant, investigate the active metabolites present in the roots using UPLC/MS-MS, isolate and elucidate the major coumarin Xanthotoxin, and predict its oral bioavailability and its potential biological impact on tongue papillae. The results revealed coumarins as the dominant chemical class in a positive acquisition mode, with bergaptol-O-hexoside 5%, Xanthotoxin 5.5%, and isoarnoittinin 6% being the major compounds. However, phenolics ruled in the negative mode, with p-coumaroyl tartaric acid 7%, 3,7-dimethyl quercetin 6%, and hesperidin 5% being the most prominent metabolites. Fractionation and purification of the chloroform fraction yielded Xanthotoxin as one of the main compounds, which appeared as white needle crystals (20 mg). ADME studies for oral bioavailability were performed to predict the potential properties of the compound if used orally. It was noted that it followed Lipinski’s rule of five, had just one parameter outside of the pink area in the radar plot, and was detected inside the threshold area using the boiled egg approach. In vivo, histopathological studies performed on rats showed a notable decrease in the tongue’s keratin thickness from an average of 51.1 µm to 9.1 µm and an average of 51.8 µm to 9.8 µm in fungiform and filiform cells, respectively. The results indicated that although Xanthotoxin is a well-known medical agent with several potential therapeutic activities in oral therapy, it may cause a destructive effect on the structure of the specialized mucosa of the tongue.

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“…[102] Among pyranocoumarins, the presence of selinidin is important since it is a well-known metabolite in the Apiaceae having been reported in Peucedanum austriacum (Jacq.) W.D.J.Koch, in some Angelica L. species [103][104][105] as well as in Glehnia littoralis F. Schmidt ex Miq., [106] in Zosima absinthifolia Link [107] and in Seseli gummiferum Pall. ex Sm.…”

Section: Chemotaxonomic Evaluation Of the Bunium Genus Within The Apiaceae Familymentioning

confidence: 99%

A Systematic Review on Phytochemistry, Ethnobotany and Biological Activities of the Genus Bunium L.

Mohammadhosseini

Frezza

Venditti

et al. 2021

Chemistry & Biodiversity

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The aim of this review article is to present, for the first time, an appraisal of the phytochemical, ethnobotanical and pharmacological data on Bunium species. The literature search was conducted using the Scopus, Google Scholar and PubMed databases. The genus Bunium has been found to produce both essential oil (EO), mainly comprising monoterpenes and sesquiterpenes, and non-volatile components mainly coumarins and flavonoids. There are several pharmacological activities associated with the Bunium species, especially antioxidant, antibacterial and antifungal properties. The chemotaxonomic appraisal of the phytochemical pattern of the genus is in sink with the current classification of the family. Moreover, this review confirms the significant ethnobotanical and pharmacological potential of different Bunium species.

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Two New Coumarins from the Chloroform Extract of Angelica urumiensis from Iran

Cited by 15 publications

References 11 publications

Targeted Isolation of Neuroprotective Dicoumaroyl Neolignans and Lignans from Sageretia theezans Using in Silico Molecular Network Annotation Propagation-Based Dereplication

Targeted Isolation of Neuroprotective Dicoumaroyl Neolignans and Lignans from Sageretia theezans Using in Silico Molecular Network Annotation Propagation-Based Dereplication

Ultra-Performance Liquid Chromatography Coupled with Mass Metabolic Profiling of Ammi majus Roots as Waste Product with Isolation and Assessment of Oral Mucosal Toxicity of Its Psoralen Component Xanthotoxin

A Systematic Review on Phytochemistry, Ethnobotany and Biological Activities of the Genus Bunium L.

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